4 Ways Owners Are Their Own Worst Enemy
Tom Stimson
February 17, 2023
A business owner sits at a counter with his laptop, gazing into the distance and looking frustrated.

We’ve all got problems. You do, I do, all of us.

The difference between a healthy business owner and an unhealthy business owner isn’t perfection. It’s recognizing that they’re going to have problems, but being open and active in finding solutions for them.

Quote: ISL - 2/20/23

So, what are some positive, unique traits of a healthy business owner who’s not getting in their own way?

A healthy owner understands their strategy, and they can communicate it to others in a way that makes sense. A healthy owner is great at delegating tactics. They’re great at exploring new ideas and applications. They’re willing to step in and get out as needed.

I had a client, for example, who very much met the healthy owner criteria listed above. Despite his best efforts to help his managers understand his strategy, though, he didn’t always have the right managers in place to execute it.

After a period of frustration, he realized he needed to step in and take on that management role SO THAT he could define the job better and make changes in the division to help it run better. Then needed to hire his replacement and get out.

In cases like this, sometimes the replacement manager is the same one who was there originally. But now they understand their job and their role much better.

This particular owner didn’t freeze because he didn’t have the right person in place. He stepped in, did it himself, and made it a job someone else could do. Not everyone can do this exact thing, but it’s a great example of a very healthy owner.

I always say a manager’s job is to remove obstacles for other people. Well, sometimes a manager has to remove obstacles for themselves.

Infographic: ISL - 2/20/23

Habits of the Unhealthy Owner

On the flip side, there are a number of qualities I run into that are unhealthy, but coachable.

Here are four of the most common.

1. Decision by Indecision

The unhealthy habit I see that’s probably the most difficult to overcome is the tendency to make a decision by not making a decision. In other words, to borrow from an old rock lyric, “If you choose not to decide, you still have made a choice.”

Most often, this occurs because the owner wants to get a consensus before proceeding with an idea. So, there’s lots of talk until everyone agrees, and then action can move forward.

The intent here is good. The owner is trying to protect everyone’s opinion. They’re trying not to make a mistake, and they figure the more the group talks things through, the better their chance of avoiding pitfalls.

But the fact of the matter is — and any good leader will tell you this — if you’ve got 70% or 80% of an idea and you don’t execute it, you’re wasting time. It’s better to get out there, make some good mistakes, and improve upon things as you go.

Indecision creates morale problems. It creates inertia. It’s a momentum and creative energy killer.

2. Asking for but Ignoring Recommendations

Another habit I see is asking for recommendations, but not trying them. Managers create and turn in reports and ideas and budgets for things that were requested, but then those things never get talked about again.

Now, maybe there’s a reason for not moving on an idea. Maybe it was too big, or too expensive, or too scary. But the fact is that you did ask for those recommendations. So at least take the time to discuss what your manager took the time to put together.

3. Waiting for the Perfect Solution

This falls into a similar category as decision by indecision, but it’s even worse. You’re waiting for a perfect solution before you do anything.

In decision by indecision, at least there was a default choice made. Here, you’re not making a choice on purpose until the perfect solution comes along.

To illustrate, I once chose not to work with a company because of something they told me during the discovery process: They had been evaluating rental management software for seven years, but had never started using one. Instead, they were using an unsupported free demo.

I had to tell them that I couldn’t help them. They were waiting for a perfect solution where there wasn’t one.

With the experience I have now, I realize that waiting for the perfect solution is a coachable problem. But it’s daunting, because if the perfect solution is the only one that’s going to work for you, chances are you’re not going to hire me anyway.

4. Plunging Ahead Without Buy-In

Conversely, there’s an unhealthy habit that’s the opposite of waiting for the perfect solution. It’s plunging ahead without buy-in.

Getting buy-in doesn’t necessarily mean getting a consensus.

Buy-in means getting input, hearing concerns, and having discussions about how those concerns can be overcome. You can’t skip that process, say Here’s how we’re going to do it, and shove something out to your team. If you do, you’ve all but guaranteed resistance, which means slower implementation and less successful use of the idea.

Facts, Discussion, Observation

Diagram: ISL - 2/20/23

In the above Venn diagram, the three intersecting circles are Facts, Observation, and Discussion. They all intersect at Clear Choices, Next Steps, and Teamwork, because when Facts, Observation, and Discussion intersect, you’re going to make Clear Choices, understand your Next Steps, and do it all with Teamwork.

On the other hand, if Facts, Discussion, and Observation fail to intersect, it leads to confusion.

Without Facts, you get Indecision. If you’re missing Discussion, you get Resistance. And a lack of Observation leads to Disruption.

A healthy owner will use the tools of Facts, Discussion, and Observation in tandem to make healthy progress. That’s what I coach clients to do for any given decision point: Make sure you have the Facts, you’ve made Observations about the need, and you’ve had a Discussion with your team.

Out of that, you get Clearer Choices, better understanding of the Next Steps, and great Teamwork.


Taken together, all of this comes down to having the right level of give and take. It also means owners will have to say yes to things they’re not necessarily comfortable with from time to time.

But being uncomfortable now and then can be very healthy.

About Tom Stimson
Tom Stimson MBA, CTS is an authority on business and strategy for small- to medium-sized companies. He is an expert on project-based selling and a thought leader for innovative business processes.
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